Skylar Grey: The Changeling

The radical transformation of the woman behind some of hip-hop's biggest hits.

The radical transformation of the woman behind some of hip-hop’s biggest hits.

Holly Brook didn’t have a problem fitting in. Instead, as a prim singer-songwriter who cooed chamomile lullabies in a lilting voice, she fit in so well that she never got noticed — not even after appearing on a hit single. In 2004 she signed with Linkin Park’s vanity imprint, Machine Shop, and the following year sang the chorus on “Where’d You Go,” a track from Mike Shinoda’s Fort Minor project that went Top 10. Sensing heat, the label rush-released her debut album, Like Blood Like Honey.

But Fort Minor fans weren’t Holly Brook fans, and the album stiffed. Released from her deal, the red-haired, green-eyed ingénue wandered from Los Angeles to Oakview, California. She took a room in a house infested with black widow spiders and worked odd jobs — including editing porn videos — while waiting for the occasional gig as an opening act, a 20-year-old with a stillborn career.

Skylar Grey has had an easier time. Even before landing a record deal, she sang the hook on Dr. Dre’s “I Need a Doctor” and appeared on Diddy Dirty Money’s “Coming Home,” both of which she cowrote. Grammy-nominated for cowriting Eminem’s No. 1 “Love the Way You Lie,” in February she performed with Dre and Shady on the awards telecast. This month she’ll play one of her first public gigs at Lollapalooza. As a vaguely goth chick able to add feminine pathos to songs in which hip-hop heavies declare vulnerability, the raven-haired, green-eyed singer has built her own successful niche. When her as-yet-untitled debut arrives in early fall, it’ll likely do more business in its first week than Holly Brook’s album has in five years. That notion makes Grey smile. Not because she’s gloating, but because she and Holly Brook are one, if not the same.

“I’m proud of the music I used to make,” says Grey, born Holly Brook Hafermann in Mazomanie, Wisconsin. “But I was capable of things that I couldn’t do while I was her.” She’s sitting in the spin offices in Manhattan on a sparkling May afternoon. Dressed in a thermal sweater and black jeans, Grey, now 25, speaks between spoonfuls of Starbucks oatmeal. “I wasn’t smart,” she says. “I made this quiet album after being on a pop radio hit. I didn’t know how to be authentic and sound pop. But before I could, I had to fix a lot about myself.”

As a child Grey toured singing folkmusic with her mother. (Her father sang in a barbershop quartet.) At 17, she quit school and decamped to Venice Beach. At 18, she had a record deal. “But when the sales numbers for my album came in,” she says, “the budget went cold. There was no ‘I’m going to hustle this record because I believe in it.’?”

Like Blood, which ultimately sold 30,000 copies, had its admirers, among them singer-composer Duncan Sheik, who took Grey on tour in 2009 and helped finance a follow-up. It was never released. “There was legal wrangling,” he says. “But any friction is history. ?Really, she hadn’t found the right context for her music. Now she has.”

Grey discovered the first clues to its location at an artist’s retreat in Oregon, where she was living after the Sheik project collapsed. There, she worked on new material — and herself. “Everyone lives alone for the first time and become a new person,” she explains. Inspired by the overcast weather, she rechristened herself Skylar Grey.

Upon leaving Oregon, she met with her publisher, Jennifer Blakeman at Universal, and explained that she needed help presenting her new music in a more saleable fashion. Blakeman suggested British producer Alex Da Kid, fresh from concocting the B.o.B-Hayley Williams smash “Airplanes.” At her urging, Alex sent Grey a beat. Fifteen minutes after hearing it, says Grey, “I’d written the chorus to ‘Love the Way You Lie.’?” Their partnership quickly yielded the choruses snapped up by Diddy and Dre.

Finished with lunch, Grey opens a MacBook and plays snippets from her new album. (She won’t confirm titles or lyrics, saying both might change.) In the silvery choruses and dramatic beats it’s easy to hear sales potential and soul. And if talk of crossover and transformation seems calculated, well, “I don’t worry about it,” she says. “I need to do what I need to do to make a living.” She flips the bird at some imagined haters.

It’s time to leave. Interscope chairman Jimmy Iovine is due to call with his pick for the first single. “I’m good at making music,” she says, slipping on her sunglasses. “It’s the only thing I’m good at. I have to make it work. Hate me if you will, but it’s my life.”

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